Vanillic acid
| Vanillic acid[1] |
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4-Hydroxy-3-methoxybenzoic acid
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Other names
4-Hydroxy-m-anisic acid, Vanillate
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| Identifiers |
| CAS number |
121-34-6 Y |
| PubChem |
8468 |
| ChemSpider |
8155 Y |
| ChEBI |
CHEBI:30816 N |
| ChEMBL |
CHEMBL120568 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11) Y
Key: WKOLLVMJNQIZCI-UHFFFAOYSA-N Y
InChI=1/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
Key: WKOLLVMJNQIZCI-UHFFFAOYAH
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| Properties |
| Molecular formula |
C8H8O4 |
| Molar mass |
168.14 g/mol |
| Appearance |
White to light yellow powder or crystals |
| Melting point |
210–213 °C
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| Hazards |
| NFPA 704 |
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N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
Vanillic acid (4-hydroxy-3-methoxybenzoic acid) is a dihydroxybenzoic acid derivative used as a flavoring agent. It is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid.[2][3]
Occurrence in nature
The highest amount of vanillic acid in plants known so far is found in the root of Angelica sinensis,[4], a herb indigenous to China, which is used in traditional Chinese medicine.
Açaí oil, obtained from the fruit of the açaí palm (Euterpe oleracea), is rich in vanillic acid (1,616 +/- 94 mg/kg).[5]
Metabolism
Vanillic acid is one of the main catechins metabolites found in humans after consumption of green tea infusions.[6]
References
- ^ "Vanillic acid (4-hydroxy-3-methoxybenzoic acid)". chemicalland21.com. http://chemicalland21.com/lifescience/foco/VANILLIC%20ACID.htm. Retrieved 2009-01-28.
- ^ Lesage-Meessen L, Delattre M, Haon M, Thibault JF, Ceccaldi BC, Brunerie P, Asther M (October 1996). "A two-step bioconversion process for vanillin production from ferulic acid combining Aspergillus niger and Pycnoporus cinnabarinus". J. Biotechnol. 50 (2–3): 107–13. doi:10.1016/0168-1656(96)01552-0. PMID 8987621.
- ^ Civolani C, Barghini P, Roncetti AR, Ruzzi M, Schiesser A (June 2000). "Bioconversion of ferulic acid into vanillic acid by means of a vanillate-negative mutant of Pseudomonas fluorescens strain BF13". Appl. Environ. Microbiol. 66 (6): 2311–7. doi:10.1128/AEM.66.6.2311-2317.2000. PMC 110519. PMID 10831404. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=110519.
- ^ Duke, JA (1992). Handbook of phytochemical constituents of GRAS herbs and other economic plants. CRC Press, 999 edition. ISBN 978-0849338656. http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?VANILICACID.
- ^ Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)". J Agric Food Chem 56 (12): 4631–6. doi:10.1021/jf800161u. PMID 18522407.
- ^ Catechin metabolites after intake of green tea infusions. P. G. Pietta, P. Simonetti, C. Gardana, A. Brusamolino, P. Morazzoni and E. Bombardelli, BioFactors, 1998, Volume 8, Issue 1-2, pp. 111–118,doi:10.1002/biof.5520080119
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| Aglycones |
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| Examples |
Burkinabin A | B | C | Galloyl glucose | Digalloyl glucose | Trigalloyl glucose: 1,2,6-Trigalloyl glucose / 1,3,6,-Trigalloyl glucose ( Corilagin) | Tetragalloyl glucose: 1,2,3,6-tetragalloylglucose | Pentagalloyl glucose: 1,2,3,4,6-pentagalloyl-glucose and 6-digalloyl-1,2,3-trigalloyl-glucose | Hexagalloyl glucose | Heptagalloyl glucose | Octagalloyl glucose | Nonagalloyl glucose | Decagalloyl glucose | 1,3,4-Tri-O-galloylquinic acid | 3,4,5-Tri-O-galloylquinic acid | 3,5-di-O-galloyl-shikimic acid | 3,4,5-tri-O-galloylshikimic acid | 1,2,6-trigalloyl alloside | 1,3,6-trigalloyl alloside | 1,2,3,6-tetragalloyl alloside |
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